2-(2,4-difluorophenyl)-1,3-bis(1H-1,2,4-triazol-1-yl)propan-2-ol

• ChemBase ID: 81
• Molecular Formular: C13H12F2N6O
• Molecular Mass: 306.2707864
• Monoisotopic Mass: 306.10406547
• SMILES: Fc1c(C(O)(Cn2ncnc2)Cn2ncnc2)ccc(F)c1
• Canonical SMILES: Fc1ccc(c(c1)F)C(Cn1cncn1)(Cn1cncn1)O
• InChI: InChI=1S/C13H12F2N6O/c14-10-1-2-11(12(15)3-10)13(22,4-20-8-16-6-18-20)5-21-9-17-7-19-21/h1-3,6-9,22H,4-5H2
• InChIKey: RFHAOTPXVQNOHP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(2,4-difluorophenyl)-1,3-bis(1H-1,2,4-triazol-1-yl)propan-2-ol
• IUPAC Traditional name: fluconazole; 2-(2,4-difluorophenyl)-1,3-bis(1H-1,2,4-triazol-1-yl)propan-2-ol
• Brand Name: Biocanol; Biozolene; Diflucan; Elazor; Flucazol; Flucostat; Flukezol; Flunizol; Flusol; Pritenzol; Triflucan
• Synonyms: α-(2,4-Difluorophenyl)-α-(1H-1,2,4-triazol-1-ylmethyl)-1H-1,2,4-triazol-1-ethanol; 1-(2,4-Difluorophenyl)-1,1-bis[(1H-1,2,4-triazol-1-yl)methyl]methanol; Biozolene; Difluconazole; Elazor; Fluconal; Flucostat; Flumycon; Flunazol; Flusol; Fluzon; Triflucan; UK 49858; Zoltec; 2-(2,4-Difluorophenyl)-1,3-bis(1H-1,2,4-triazol-1-yl)propan-2-ol; Fluconazole; 2-(2,4-difluorophenyl)-1,3-di(1H-1,2,4-triazol-1-yl)propan-2-ol; 2,4-difluoro-,1-bis(1H-1,2,4-triazol-1-ylmethyl)benzyl alcohol; Fluconazole; Diflucan; Trican; Alfumet; 2-(2,4-difluorophenyl)-1,3-bis(1H-1,2,4-triazol-1-yl)propan-2-ol; Fungata

Database IDs

• CAS Number: 86386-73-4
• MDL Number: MFCD00274549
• PubChem SID: 46505735; 24724485; 160963544
• PubChem CID: 3365

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.707209
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 0.5604975
• LogD (pH = 7.4): 0.56095034
• Log P: 0.56095827
• Molar Refractivity: 97.1995 cm^3
• Polarizability: 26.91871 Å^3
• Polar Surface Area: 81.65 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.58
• LOG S: -2.34
• Solubility (Water): 1.39e+00 g/l

PROPERTIES

Physical Property

• Solubility: 1 mg/L; DMSO: soluble5 mg/mL; Ethyl Acetate; Methanol
• Apperance: powder; White to Off-White Solid
• Melting Point: 138-140°C
• Hydrophobicity(logP): 0.4; -0.44

Safety Information

• Storage Condition: -20°C; -20°C Freezer; Room Temperature (15-30°C)
• RTECS: XZ4810000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: room temp

Pharmacology Properties

• Target: P450
• Gene Information: human ... CYP1A2(1544)
• Mechanism of Action: Inhibitor of fungal cytochrome P450 enzyme 14alpha-demethylase

Product Information

• Purity: ≥98% (HPLC); 95%
• Grade: certified reference material
• Salt Data: Free Base
• Packaging: pkg of 1 g
• Application(s): Antifungal agent; Effective in single oral dose against vaginal candidiasis; Not active against Aspergillus; Prophylactic treatment for AIDS patients
• Pharmacopeia Traceability: traceable to USP 1271700
• Empirical Formula (Hill Notation): C13H12F2N6O

DETAILS

MP Biomedicals - 02198986

A highly selective inhibitor of fungal cytochrome P-450 sterol C-14 α-demethylation.

DrugBank - DB00196

• Drug Groups: approved
• Description: Triazole antifungal agent that is used to treat oropharyngeal candidiasis and cryptococcal meningitis in AIDS. [PubChem]
• Indication: For the treatment of fungal infections.
• Pharmacology: Fluconazole, a synthetic antifungal agent of the imidazole class, is used to treat vaginal candidiasis. It inhibits the fungal lanosterol 14 alpha-demethylase which thereby prevents the formation of ergosterol which is an essential component in the fungal cell membrane.
• Toxicity: Symptoms of overdose include hallucinations and paranoid behavior.
• Affected Organisms: Fungi
• Biotransformation: Hepatic
• Absorption: 90%
• Half Life: 30 hours (range 20-50 hours)
• Protein Binding: 11 to 12%
• Elimination: In normal volunteers, fluconazole is cleared primarily by renal excretion, with approximately 80% of the administered dose appearing in the urine as unchanged drug.
• Clearance: * 0.23 mL/min/Kg [adults]; * 0.18 mL/min/Kg [In premature newborns within 36 hours of birth]; * 0.22 mL/min/Kg [In premature newborns 6 days old]; * 0.33 mL/min/Kg [In premature newborns 12 days old]; * 0.4 mL/min/kg [9 Months-13 yearsreceiving single-oral 2 mg/kg]; * 0.51 mL/min/Kg [9 Months-13 yearsreceiving single-oral 8 mg/kg]; * 0.49 mL/min/Kg [5-15 yearsreceiving multiple IV 2 mg/kg]; * 0.59 mL/min/Kg [5-15 yearsreceiving multiple IV 4 mg/kg]; * 0.66 mL/min/Kg [5-15 yearsreceiving multiple IV 8 mg/kg]
• External Links: Wikipedia; RxList; Drugs.com

Selleck Chemicals - S1331

Research Area: Immunology , Infection
Biological Activity:
Fluconazole is used to treat serious fungal or yeast infections, such as vaginal candidiasis, oropharyngeal candidiasis, esophageal candidiasis, other candida infections, or fungal meningitis. This medicine works by killing the fungus or yeast, or preventing its growth. [1]Fluconazole is also used to prevent candidiasis in patients having bone marrow transplants, who receive cancer or radiation treatment.[1]

Sigma Aldrich - F8929

Biochem/physiol Actions
Fluconazole is an antifungal agent. It is highly selective inhibitor of fungal cytochrome P-450 sterol C-14 α-demethyllation. Fluconazole is a potent inhibitor of CYP2C9. Fluconazole interferes with fungal ergosterol synthesis and downregulates the metallothionein gene.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. F8929.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - PHR1160

General description
This certified reference material (CRM) is produced and certified in accordance with ISO/IEC 17025 and ISO Guide 34.
Other Notes
Values of analytes vary lot to lot.
Biochem/physiol Actions
Fluconazole is an antifungal agent. It is highly selective inhibitor of fungal cytochrome P-450 sterol C-14 α-demethyllation. Fluconazole is a potent inhibitor of CYP2C9. Fluconazole interferes with fungal ergosterol synthesis and downregulates the metallothionein gene.

Toronto Research Chemicals - F421000

Used as an antifungal.

REFERENCES

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